tert-Butanol → (3-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamic Acid Tert-Butyl Ester

HRID 34109Notes

Reaction equation

HRID 34109 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[C:8](C(O)=O)[CH:9]=2)[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.C([N:52]([CH2:55]C)CC)C.[C:57]([OH:61])([CH3:60])([CH3:59])[CH3:58]>C(OCC)(=O)C>[C:57]([O:61][C:55](=[O:40])[NH:52][C:8]1[CH:9]=[C:10]2[C:2]([I:1])=[N:3][N:4]([C:14]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:5]2=[CH:6][N:7]=1)([CH3:60])([CH3:59])[CH3:58]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 689282723-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carboxylic Acid

Product 1

HCID 68926908(3-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1.0 g of 3-iodo-1-trityl-1H-pyrazolo[3,4-c]pyridine-5-carboxylic acid in tert-butanol were added 0.57 g of diphenylphosphoryl azide and 0.31 mL of triethylamine at room temperature, and heated at reflux for 6 hours. The solution was diluted with ethyl acetate, the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10), to afford 455 mg of the title compound as colorless crystals.

Workup

  1. temperatureheated
  2. temperatureat reflux for 6 hours
  3. washthe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe crude product was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10)

Sources & evidence

ORD record
ord-5b1fdf1c5f444172b21fe5c75634ad0f
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

Loading…